UA122897C2 - Спосіб одержання циклогексанону з фенолу - Google Patents
Спосіб одержання циклогексанону з фенолу Download PDFInfo
- Publication number
- UA122897C2 UA122897C2 UAA201705673A UAA201705673A UA122897C2 UA 122897 C2 UA122897 C2 UA 122897C2 UA A201705673 A UAA201705673 A UA A201705673A UA A201705673 A UAA201705673 A UA A201705673A UA 122897 C2 UA122897 C2 UA 122897C2
- Authority
- UA
- Ukraine
- Prior art keywords
- phenol
- section
- cyclohexanone
- cyclohexanol
- pipe
- Prior art date
Links
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 title claims abstract description 379
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 title claims abstract description 272
- 238000000034 method Methods 0.000 title claims abstract description 88
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 20
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 claims abstract description 160
- 238000005984 hydrogenation reaction Methods 0.000 claims abstract description 144
- 238000004821 distillation Methods 0.000 claims abstract description 92
- 239000001257 hydrogen Substances 0.000 claims abstract description 84
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 84
- 238000000926 separation method Methods 0.000 claims abstract description 47
- 238000000746 purification Methods 0.000 claims abstract description 39
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 61
- 238000006356 dehydrogenation reaction Methods 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 42
- 239000003054 catalyst Substances 0.000 claims description 33
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 22
- 239000012071 phase Substances 0.000 claims description 21
- 238000005265 energy consumption Methods 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 229910052763 palladium Inorganic materials 0.000 claims description 11
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 claims description 7
- 229910052697 platinum Inorganic materials 0.000 claims description 7
- 239000012808 vapor phase Substances 0.000 claims description 7
- 238000009835 boiling Methods 0.000 claims description 6
- 238000011437 continuous method Methods 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 2
- AFJYYKSVHJGXSN-KAJWKRCWSA-N selamectin Chemical compound O1[C@@H](C)[C@H](O)[C@@H](OC)C[C@@H]1O[C@@H]1C(/C)=C/C[C@@H](O[C@]2(O[C@@H]([C@@H](C)CC2)C2CCCCC2)C2)C[C@@H]2OC(=O)[C@@H]([C@]23O)C=C(C)C(=N\O)/[C@H]3OC\C2=C/C=C/[C@@H]1C AFJYYKSVHJGXSN-KAJWKRCWSA-N 0.000 claims 1
- 238000011084 recovery Methods 0.000 abstract description 3
- 238000010924 continuous production Methods 0.000 abstract description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000000047 product Substances 0.000 description 70
- 150000002431 hydrogen Chemical class 0.000 description 31
- 238000010438 heat treatment Methods 0.000 description 30
- 239000008246 gaseous mixture Substances 0.000 description 25
- 239000007788 liquid Substances 0.000 description 25
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 239000012074 organic phase Substances 0.000 description 20
- 238000001704 evaporation Methods 0.000 description 19
- 238000009833 condensation Methods 0.000 description 16
- 230000005494 condensation Effects 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 13
- 238000003860 storage Methods 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 239000013067 intermediate product Substances 0.000 description 10
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 10
- 239000007792 gaseous phase Substances 0.000 description 9
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 230000006835 compression Effects 0.000 description 6
- 238000007906 compression Methods 0.000 description 6
- 239000012467 final product Substances 0.000 description 6
- 238000003973 irrigation Methods 0.000 description 5
- 230000002262 irrigation Effects 0.000 description 5
- 238000002955 isolation Methods 0.000 description 5
- 239000003463 adsorbent Substances 0.000 description 4
- 239000006227 byproduct Substances 0.000 description 4
- 239000002826 coolant Substances 0.000 description 4
- 229910001873 dinitrogen Inorganic materials 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000007791 liquid phase Substances 0.000 description 4
- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 239000004677 Nylon Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 239000003990 capacitor Substances 0.000 description 3
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 230000007423 decrease Effects 0.000 description 3
- 238000010586 diagram Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- 229920001778 nylon Polymers 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 150000001342 alkaline earth metals Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 230000010354 integration Effects 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000010926 purge Methods 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 102220481794 Kinesin-like protein KIF20A_I61Y_mutation Human genes 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 229920002302 Nylon 6,6 Polymers 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000012190 activator Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 description 1
- 229910000287 alkaline earth metal oxide Inorganic materials 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000498 cooling water Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- -1 cyclohexanol Chemical compound 0.000 description 1
- HPXRVTGHNJAIIH-PTQBSOBMSA-N cyclohexanol Chemical class O[13CH]1CCCCC1 HPXRVTGHNJAIIH-PTQBSOBMSA-N 0.000 description 1
- PWVHLUKAENFZIA-UHFFFAOYSA-N cyclohexanol;cyclohexanone Chemical compound OC1CCCCC1.O=C1CCCCC1 PWVHLUKAENFZIA-UHFFFAOYSA-N 0.000 description 1
- 230000009849 deactivation Effects 0.000 description 1
- 238000005868 electrolysis reaction Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000010574 gas phase reaction Methods 0.000 description 1
- 230000020169 heat generation Effects 0.000 description 1
- 239000004434 industrial solvent Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 229910052741 iridium Inorganic materials 0.000 description 1
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 1
- 229910001338 liquidmetal Inorganic materials 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910052762 osmium Inorganic materials 0.000 description 1
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000002407 reforming Methods 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 238000009834 vaporization Methods 0.000 description 1
- 230000008016 vaporization Effects 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002912 waste gas Substances 0.000 description 1
- 238000004065 wastewater treatment Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/006—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by hydrogenation of aromatic hydroxy compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J21/00—Catalysts comprising the elements, oxides, or hydroxides of magnesium, boron, aluminium, carbon, silicon, titanium, zirconium, or hafnium
- B01J21/02—Boron or aluminium; Oxides or hydroxides thereof
- B01J21/04—Alumina
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
- B01J23/44—Palladium
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/17—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds
- C07C29/19—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings
- C07C29/20—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by hydrogenation of carbon-to-carbon double or triple bonds in six-membered aromatic rings in a non-condensed rings substituted with hydroxy groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/74—Separation; Purification; Use of additives, e.g. for stabilisation
- C07C29/76—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment
- C07C29/80—Separation; Purification; Use of additives, e.g. for stabilisation by physical treatment by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C35/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring
- C07C35/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic
- C07C35/08—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a ring other than a six-membered aromatic ring monocyclic containing a six-membered rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C39/00—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring
- C07C39/02—Compounds having at least one hydroxy or O-metal group bound to a carbon atom of a six-membered aromatic ring monocyclic with no unsaturation outside the aromatic ring
- C07C39/04—Phenol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/002—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by dehydrogenation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
- C07C45/78—Separation; Purification; Stabilisation; Use of additives
- C07C45/81—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation
- C07C45/82—Separation; Purification; Stabilisation; Use of additives by change in the physical state, e.g. crystallisation by distillation
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
- C07C49/385—Saturated compounds containing a keto group being part of a ring
- C07C49/403—Saturated compounds containing a keto group being part of a ring of a six-membered ring
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2219/00—Chemical, physical or physico-chemical processes in general; Their relevant apparatus
- B01J2219/00002—Chemical plants
- B01J2219/00027—Process aspects
- B01J2219/00033—Continuous processes
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP14192423 | 2014-11-10 | ||
| EP2015075113 | 2015-10-29 | ||
| PCT/EP2015/075951 WO2016075047A1 (en) | 2014-11-10 | 2015-11-06 | Process for the production of cyclohexanone from phenol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| UA122897C2 true UA122897C2 (uk) | 2021-01-20 |
Family
ID=55953768
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| UAA201705673A UA122897C2 (uk) | 2014-11-10 | 2015-11-06 | Спосіб одержання циклогексанону з фенолу |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US10301243B2 (es) |
| EP (1) | EP3218338B1 (es) |
| JP (1) | JP6249467B1 (es) |
| KR (1) | KR101820639B1 (es) |
| CN (1) | CN107124881B (es) |
| EA (1) | EA031615B1 (es) |
| ES (1) | ES2803082T3 (es) |
| MX (1) | MX2017006073A (es) |
| PL (1) | PL3218338T3 (es) |
| SA (1) | SA517381498B1 (es) |
| UA (1) | UA122897C2 (es) |
| WO (1) | WO2016075047A1 (es) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110563564B (zh) * | 2018-06-06 | 2022-02-01 | 中国石油化工股份有限公司 | 苯酚加氢制备环己酮的方法 |
| CN108816223B (zh) * | 2018-07-09 | 2021-08-20 | 江苏凌飞科技股份有限公司 | 一种制备壬基环己醇聚氧乙烯醚用的催化剂及其制备方法 |
| CN110372462A (zh) * | 2019-08-06 | 2019-10-25 | 吉林凯莱英医药化学有限公司 | 连续化合成-纯化一体装置及含有其的连续化反应系统 |
| EP4288401A1 (en) | 2021-02-04 | 2023-12-13 | Cap Iii B.V. | Process control for the hydrogenation of phenol |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2829166A (en) | 1933-04-04 | 1958-04-01 | Allied Chem & Dye Corp | Hydrogenation of phenol |
| US5015787A (en) | 1989-04-10 | 1991-05-14 | Allied-Signal Inc. | Process for production cyclohexanol |
| EA201001033A1 (ru) * | 2007-12-20 | 2010-12-30 | ДСМ АйПи АССЕТС Б.В. | Способ получения циклогексанона с модифицированной пост-дистилляцией |
| ATE544741T1 (de) | 2007-12-20 | 2012-02-15 | Dsm Ip Assets Bv | Verfahren zur herstellung von cyclohexanon mit mehrfacher nachdestillation |
| EP2231578A1 (en) * | 2007-12-20 | 2010-09-29 | DSM IP Assets B.V. | Cyclohexanone production process with impurities removal |
| WO2014001461A1 (en) | 2012-06-28 | 2014-01-03 | Dsm Ip Assets B.V. | Process for the production of a mixture comprising cyclohexanone and cyclohexanol from phenol |
| WO2014163080A1 (ja) * | 2013-04-05 | 2014-10-09 | 三井化学株式会社 | シクロヘキサノン化合物の製造方法 |
| US20160368844A1 (en) | 2013-07-24 | 2016-12-22 | Exxonmobil Chemical Patents Inc. | Process for Producing Mixtures of Cyclohexanone and Cyclohexanol |
| WO2016053581A1 (en) | 2014-09-30 | 2016-04-07 | Exxonmobil Chemical Patents Inc. | Process for making cyclohexanone |
-
2015
- 2015-11-06 JP JP2017543886A patent/JP6249467B1/ja active Active
- 2015-11-06 EA EA201791013A patent/EA031615B1/ru not_active IP Right Cessation
- 2015-11-06 MX MX2017006073A patent/MX2017006073A/es unknown
- 2015-11-06 ES ES15790590T patent/ES2803082T3/es active Active
- 2015-11-06 UA UAA201705673A patent/UA122897C2/uk unknown
- 2015-11-06 PL PL15790590T patent/PL3218338T3/pl unknown
- 2015-11-06 US US15/525,448 patent/US10301243B2/en active Active
- 2015-11-06 KR KR1020177015774A patent/KR101820639B1/ko active IP Right Grant
- 2015-11-06 EP EP15790590.2A patent/EP3218338B1/en active Active
- 2015-11-06 WO PCT/EP2015/075951 patent/WO2016075047A1/en active Application Filing
- 2015-11-06 CN CN201580060894.6A patent/CN107124881B/zh active Active
-
2017
- 2017-05-10 SA SA517381498A patent/SA517381498B1/ar unknown
Also Published As
| Publication number | Publication date |
|---|---|
| CN107124881B (zh) | 2019-04-19 |
| EA031615B1 (ru) | 2019-01-31 |
| EP3218338A1 (en) | 2017-09-20 |
| JP6249467B1 (ja) | 2017-12-20 |
| PL3218338T3 (pl) | 2020-09-21 |
| EP3218338B1 (en) | 2020-06-10 |
| KR20170077249A (ko) | 2017-07-05 |
| ES2803082T3 (es) | 2021-01-22 |
| JP2018501301A (ja) | 2018-01-18 |
| WO2016075047A1 (en) | 2016-05-19 |
| EA201791013A1 (ru) | 2017-12-29 |
| US20180290955A1 (en) | 2018-10-11 |
| CN107124881A (zh) | 2017-09-01 |
| KR101820639B1 (ko) | 2018-01-19 |
| SA517381498B1 (ar) | 2020-09-03 |
| US10301243B2 (en) | 2019-05-28 |
| MX2017006073A (es) | 2018-01-11 |
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